The Ill Fated Romance of Stefan Salvatore
by justareader13
Summary: Have you ever wondered if Stefan ever loved someone before Katherine came along? Here's the story of Stefan and Arabella. Follow them as they love each other despite their obvious differences.


**I DISCLAIM EVERYTHING HERE**

**Spoilers: from the Stefan Diaries: Origins and S1 of TVD**

**Pairings: mainly Stefan/OC, Stefan/Rosalyn & Rosalyn/OC mentions of Stefan/Katherine **

**AN: I picture the OFC (Arabella) as Tika Sumpter, Rosalyn (from the Stefan Diaries) as Dianna Agron, Cordelia (from the Stefan Diaries) as Viola Davis and OMC (William) as Adam Brody. There are pictures on my profile.**

Caroline stared at Stefan undecidedly. She had often wondered about his life before Katherine, she had even worked up the nerve to ask him a few things. She knew he and Damon were close, she knew his mother died when he was eight after having been sick after giving birth to him and he didn't really like talking about it, he spoke about his father's attitude towards him and Damon and spoke about his father keeping slaves. He talked fondly about the slave, Cordelia, who had for the most part raised him and Damon while their mother was sick and their father was either drunk or didn't care but she never seemed to be able to get this question out

"What is it?" Stefan asked concerned, turning away from his animated conversation with Klaus after noticing her eyes that were glued to his face.

"Nothing, it's nothing." Caroline said shrugging it off

"Really? Because the hole you were staring into poor Stefan's face begged to differ." Klaus said to her sipping on the drink in his hand

"It's just, well I was wondering…"

"Go ahead Care; you know you can ask me anything." Stefan said to her

"Did you have any… relationships before Katherine?" She asked awkwardly

"Where's this coming from?" he asked surprised

"I've actually been thinking about this for a while and Bonnie and I were talking and she told me about some relationships Damon told her about before Katherine but they were nothing serious and so I thought about you."

"I'm actually curious to know the answer to this question as well." Klaus said getting comfortable in the couch of his living room

Stefan looked from Klaus' expression of anticipation to Caroline's hopeful expression before launching into his tale.

_**Mystic Falls, Virginia, June 19 1863**_

_Sixteen year old Stefan Salvatore was tapping his foot against the hardwood floor. He ignored the looks his father was giving him as a result and went right along doing it._

"_Stefan Lorenzo Salvatore if you do not stop that infernal foot tapping I will—", Giuseppe's threat was cut off by the tolling of the clock which sent Stefan to his feet running out the door yelling behind him,_

"_I'm going to see Rosalyn." He ran out to the field greeting various servants and slaves and making sure to stop and kiss Miss Cordelia on her dark chocolate hued cheek before sprinting off into the forest. He was not on his way to see Rosalyn, though he supposed he should pay his fiancée a visit eventually, he was on his way to see the woman he really loved, Arabella. _

_The girl used to be a slave on the Salvatore Estate when they were young; he remembered playing with her almost every day. His mother had shown Arabella great favor, especially since the girl's mother died giving birth to her. Elizabeth Salvatore knew she would die eventually from the complications that arose when she gave birth to Stefan and she had always wanted a girl so she fashioned herself into a surrogate mother, even naming Arabella which means 'answered prayer'. Giuseppe sold Arabella to the Cartwrights first chance he got following his wife's death. Seeing her again stirred some rebellious, lonely and sheltered part of Stefan. He was sad almost all the time nowadays since Damon had gone off to war and spending time with the workers on his estate helped but he never knew you could be surrounded by people and still be feeling so alone until Damon left. Then Arabella came around and he had something else to focus on other than waiting to hear if his brother was killed in action and planning a marriage with a girl who he didn't love in the romantic sense of the word. He didn't expect to fall so hard for Arabella but there was no turning back now._

_He kept running then stopped abruptly, keeping low to the ground as he came up to a picturesque clearing complete with green fields, a waterfall and a rippling lake which housed various moss infested boulders. He peeked through the tree branches and on one of the rocks he saw her sitting and waiting for him. Her dark chocolate toned skin seemed to make her glitter in the sun, her naturally curly, dark brown hair was left to blow freely in the wind, her lips were pulled into a smile as she observed the butterfly perched on her delicate fingers and the brown pools of light that were her eyes radiated laughter as the butterfly hopped from one finger to the other. She was an exceptional beauty and worth more than anyone had ever given her just because her skin tone was darker than others._

"_Arabella." He called stepping from the trees to reveal his self to her. Her smile grew tenfold as she stood up. She let the butterfly fly away and she closed the distance between them and pressed her lips chastely to his and he deepened the kiss instantly. She was always timid with him and never wanted to push. Afraid that she would cross a line and he would hurt her but he never, ever would and he'd keep telling her until she believed it both in her heart and her mind. He pulled his lips from hers to press his forehead against hers breathlessly_

"_I've missed you more than I can articulate. I feel like it's been a millennia since last we met." Stefan said to her, she smiled softly_

"_Just a bit dramatic don't you think?" She said to him in her sweet voice_

"_Not at all, there is no greater yearning compared to how I yearn just to be in your presence." He said smoothly back to her, knowing she was a hopeless romantic and how much she loved to hear such things and she deserved to hear them everyday. He wished she never doubted her beauty but she did; so he made it his mission that as soon as he saw her he would make sure to let her know how much she was loved before she let any wayward thoughts grab hold of her mind and manifest within her_

"_Oh really? More than a starving man misses food?" she questioned playfully_

"_My heart would hurt a thousand times more than his stomach if I were to lose you." Her smile got larger as her heart beat faster_

"_More than a horse walking through the desert misses water?"_

"_My whole being dries up when you're not near, no amount of sustenance can quell the thirst for you."_

"_More than—",_

"_More than a child would miss their blanket, more than a mother would miss their child, more than the flowers that dance and bloom in the spring would miss the sun and would equally miss the rain. I love you more than words could possibly say, living without you is more painful than you can imagine." Both of their moods deflated slightly_

"_I think I might have an idea actually. I wait on baited breath, count the seconds between our meetings but..."_

"_But?" Stefan questioned, his eyes flickering to his face_

"_I think my friend grows suspicious of what I do when I leave the plantation."_

"_Does she know?"_

"_I do not think so."_

"_Even so, would it be a bad thing if she did? She would not tell Mr. Cartwright."_

"_But she may tell the other slaves and Miss Rosalyn or Mr. Cartwright could overhear." She said pulling away from his embrace and sitting on a boulder, he walked over and sat next to her _

"_I wish we didn't have to hide—" Stefan sighed _

"_But it is necessary. If they knew about us—"_

"_They would lynch you and—",_

"_Do who knows what to you." They finished each other's sentences effortlessly. They had had this conversation many times, Stefan wanted to be able to walk around town with her on his arm but she was more realistic than he and knew that that could never be, not in their lifetime anyway. _

"_Come on; let's take a walk to turn your mind from such things." Stefan said getting up and smiling at her, holding his hands out for her to take; she smiled and took it in hers, heart soaring like it did whenever he touched her._

_**July 13, 1863**_

_Stefan sat next to Rosalyn in the Founder's Council meeting bored out of his mind. They had moved on from talking supernatural creatures for which Stefan was grateful. He had yet to come across a werewolf, vampire or witch but he knew well enough that they did exist and that was really the only part of the meeting he had to be aware of. He loathed that his father dragged him to this infernal meeting, if Damon were here he would've been able to talk the two out of attending and they would've been off scot free but unfortunately his older brother was gone and as always Stefan's mood took a nose dive whenever he thought of Damon._

"_Are you alright?" He heard Rosalyn ask discreetly as the meeting waged on. He may not be in love with her any more than she was with him but she was his friend and she didn't want to be there any more than he did. They did have some things in common so what would be the point in hating her, he actually liked that they were friends, they were best friends actually_

"_Just thinking of Damon for a moment." He said sadly_

"_You know he'll be fine Stefan, don't worry yourself over such things." He gave a grunt of acceptance before the mundane droll of the meeting reached his ears again _

"_Is it me or does this meeting drag on just a bit?" He asked in a low voice_

"_Oh it's not you. It seems whenever they put one topic to rest they pull a new one out of their asses." Stefan snorted trying to stifle his laughter and tried to further cover it up by making it sound like he sneezed though from his father's glare he wasn't fooled. That was another reason he liked being Rosalyn's friend: she didn't conform to the whole notion that women were to be seen and not heard. She was brazen, bold, outspoken and resourceful and she could both out drink and out-cuss a sailor. His brother would be very fond of her._

"_You best watch your mouth, what if someone had heard you?" he said amused_

"_And what if they had? They wouldn't dare lay a pinky on me if they knew what was best for them." Another thing about Rosalyn was that she was quick to fight, whether it was a man or woman she had no qualms against putting away her petticoats and skirts in favor of riding trousers and boots and getting down and dirty with the best of them._

"_You need to calm your heated head, it won't surprise me if you go looking for a fight as soon as they let us leave."_

"_What better way to entertain myself? You could place bets and have enough money to buy me a drink when we leave here. Heaven knows I deserve a reward for my endurance during this torture." She said back enthusiastically _

"_You are going to get both of us into irrevocable trouble one day." Stefan said to her shaking his head fondly _

"_I get into trouble every day and you know you love when I drag you down with me." _

"_Oh please, your ego is almost as big as your father's beer gut." Rosalyn placed a hand over her mouth to hide the large grin on her face but the smile fell and the two's heads snapped up as the conversation took a sudden turn._

"_What of the slave wages? Are we gonna talk about that at all?" said Jonathon Gilbert. The two looked at each other warily. They were both anti-slavery and though they were told that the war was about more they still were wary of any decisions the council made in those regards. Many of their friends were slaves, people they grew up with, people who raised them, people they loved. The council had decided, following the Emancipation Proclamation, to see how many slaves left and many had. The rest had nowhere to go or just didn't believe the proclamation was legitimate so they had begun to pay the slaves for their labor._

"_And what of the wages?" Giuseppe asked_

"_Well, I feel they're too steep." Benjamin Lockwood said while some of the others spoke up to agree with him trying their best to ignore the tall, milk chocolate hued man standing by the door. He was a slave of Thomas and Honoria Fell, Stefan and Rosalyn however noticed the man's sullen face._

"_Too steep? Its two dollars a month. You could stop being so miserly and pay them or work in the fields yourself." Rosalyn said speaking up boldly and in an affronted tone, much to the shock of much of the male council members and the quiet pride of the females, Stefan had to fake sneeze again in order to keep the chuckles at bay _

"_Rosalyn! You will hold your tongue child!" Her father, Abraham Cartwright, bellowed. Stefan reigned in the laughter and decided to speak up as well_

"_It's true though, what's two dollars to us really? It isn't as if we're not all founding families here, not as if we don't all have our safes of money tucked away nice and neat. If we deny these people their fair share how are we better than the Northerners who wish to oppress us?" He said knowing he'd strike a chord if he brought the raging war up. The room had grown eerily quiet as no one knew what to say. It wasn't as if they could deny the boy's words, they were true_

"_Well, who brought these children here? Wayland, escort them out at once." Thomas said. Honoria winked at the two sixteen year olds as they begrudgingly stood up and followed the dark skinned man out of the council meeting and a little way's away. They were both a little startled when he spoke_

"_Thank ya for tryin' back there." He said with a heavier southern accent than was the norm around town_

"_No 'thank you' necessary sir." Rosalyn said to him_

"_We should be thanking you. All of you guys, without you we'd be nothing." Stefan said smiling kindly. The man smiled back and stood up straighter like he had a little more confidence in himself_

"_You'd better get back before your absence is noticed." Rosalyn said softly,_

"_And here." She said before she pulled out some chocolate in a silk cloth from a pocket she had sewed herself into her dress_

"_I saw those children on the Fell's property; would you pass this along to them please?"_

"_The Fells don't have no young'uns." The man said confused as he took the wrapped chocolate from her._

"_The children weren't theirs, they work in the fields." She said before she looped her arm into Stefan's and the two began to stroll away from the shocked man. He knew Cartwright was one of the worst masters in all of Mystic Falls, so how'd his daughter become who she was? He didn't know but he was happy as he thought of the slave children's faces lighting up as they tasted chocolate for the first time. _

"_Sometimes I think you're insane Rose." Stefan said to her_

"_And it's precisely why I'm your best friend Stef." She said back, her emerald eyes twinkling mischievously. He shook his head at her. He was engaged to her, engaged to his best friend and he loved her but wasn't in love with her and she wasn't in love with him but he still couldn't help but think if she knew about him and Arabella she'd be hurt and that's the last thing he wanted _

_**July 29, 1863**_

_Stefan and Arabella lay on a blanket looking up at the sky. The stars were sparkling and shining wonderfully, the sky was at least three different shades of blue, the grass still wet with the light rain that had fallen two hours prior, everything was so beautiful and natural. _

"_Anche l'etereo cielo notturno non è così bello come voi, il mio amore." she heard Stefan mummer_

"_Was that Italian or French?" She asked curiously rolling over onto her stomach to face him better. He smiled as his cheeks reddened. He hadn't intended to speak out loud. _

"_Italian." he said sheepishly_

"_Well, what does it mean?" She said to him, smiling at his embarrassment. He was cute when he blushed and she could see it clearly thanks to the stars and moonlight_

"_It means 'even the ethereal night sky is not as beautiful as you, my love'." He said shrugging while fidgeting with his hands. She'd never seen him so nervous but then again he had never spoken in a language other than English to her before. Though she did know his father would not stand for him not to learn Italian and he had learned French from his mother, one of the few things he'd been able to retain from her, she was intrigued that this was the first he had spoken either one to her._

"_Well, you're accent is cute but I don't know about that statement." She said, playing with one of her springy curls. He frowned as he looked at her downcast face_

"_What do you mean?"_

"_I'm not as pretty as other girls, even black ones. Even they are prettier than me, get treated better because their prettier… lighter. I'm certainly no Rosalyn Cartwright, blonde, rich, beautiful, engaged to you." _

"_Hey, you know I love Rosalyn no more than as a friend and you are one of the most beautiful, selfless, courageous, loving beings I've ever known. Why do you doubt your beauty so? It breaks my heart." Arabella sat up on her knees away from his glistening eyes as she continued to speak_

"_It's hard to think of yourself as beautiful when you can't even be seen in public with the man that you love. Rosalyn has you in a way I can't." Stefan sat up next to her, taking her face into his hands and forcing her to look at him_

"_Yet you have more of me than she could ever dream to. You own my heart. My soul and my being seek only you. My mind and body desire only you. You have wormed your way into my heart and I see no opening for you to escape, not that I'd want you to. I love you. Please do not doubt this fact." She smiled a watery smile as tears slipped down her face. He pulled her lips to his catching her in a searing kiss. He pulled her closer to him with his arm around her waist and she wrapped her arms around his neck pulling him closer, they kissed intensely like that for a few moments before he pushed her backwards onto her back and straddled her still kissing her as she wrapped her legs around his torso. Her tongue swept across his lips like a ballerina walking a tightrope and he opened his mouth to grant her access, their tongue twisting in a forbidden tango. He started to kiss down her neck and pulled some of her skin into his mouth, giving her light hickies. She moaned at the sensation. He pulled away when human necessity made itself known. He breathed heavily staring into her eyes. Both of them knew where this was going and though they'd been together for 10 months now, they hadn't had each other carnally yet._

"_Are you sure about this, Bells? I don't want to hurt you."_

"_From what I hear, I suspect that's inevitable. And I love you Stefan, there's no one else I'd rather give this part of myself to." Stefan smiled at her before his mouth went back to hers and they gave themselves to each other entirely. _

_**August 21, 1863**_

_Stefan and Arabella rode atop Mezzanotte, his black stallion. Stefan had Cordelia cover for Arabella (though she didn't know she was covering up anything). Arabella and Stefan had just shared a moonlight picnic in a clearing in the middle of the old woods. Stefan was telling her how Damon was coming home soon to celebrate Stefan's seventeenth birthday, he was so happy and animated that she couldn't help but be happy for him. She rested her head on his back and tightened her arms around his torso. She loved riding with Stefan, it made her feel alive, like they could escape this place and be happy together somewhere away from the oppression and racism and the sinister plans that others would set out for them if they knew about the two's relationship. Stefan suddenly stopped Mezzanotte._

"_What is it?" Arabella asked_

"_I hear something." Arabella suddenly heard a tinkling laughter_

"_Or rather someone," She commented. Stefan quickly directed the horse into some trees for cover so the two would be hidden. They watched as William Jones raced out of the trees pulling a giddy Rosalyn, who wore beige riding trousers and a black, wool female's blazer with a white button up under it, behind him. He swung around and kissed her full on the lips._

"_I've missed you, your dreadful father has made it impossible for us to be together in the daylight now that he wants to marry you off to Stefan Salvatore." he said _

"_Stefan is my friend, my best friend, so if you're thinking of speaking ill of him you can stop right there." She warned_

"_I know he is your friend and you love him but he is not the man you're __**in**__ love with or is there something you wish to tell me?" She stepped back glaring at him_

"_You know I'm in love with you not Stefan but this is my father's will. What am I supposed to do? I can't just run off with you, I'll bring shame to my family." She said_

"_Is it because of our social standing? My family is the poorest of the Founding Families—", He said sadly before she cut him off in a fierce tone_

"_Still yourself!" she said angrily_

"_You know I don't rate someone based on any monetary value. You are a brave, true, honest, well rounded, beautiful man and if things were different I'd already have asked you to marry me."_

"_**You**__ ask __**me**__, isn't that a little forward?" he said laughing at her words_

"_Have you ever known me to be anything but?" she said smiling, she pulled him in for another kiss but he ran off before she could. She immediately set off chasing after him, her trousers allowing for much longer strides than her gown would've. _

"_Did you know about them?" Arabella asked once Stefan directed Mezzanotte out of hiding._

"_No, though I suppose we have no room to judge." He said, pensively looking at where the two had run off. _

_**THE NEXT DAY **_

_Stefan sat across from Rosalyn who was rattling on about who she didn't want to attend their marriage, it was going to be a long engagement but they were still expected to relay certain information to their fathers. Rosalyn was enthusiastically contemplating if she could get away with beating Nicola Forbes up in her wedding dress seeing as how she wouldn't be her father's burden anymore when Stefan's voice cut her off_

"_So you and William Jones, huh?" he asked suddenly. Rosalyn's head snapped up in shock for a nanosecond before she schooled her face but it was already too late; Stefan noticed_

"_I'm sure I have no idea what you mean Stefan." She said aghast_

"_Of course you do." Was his simple reply_

"_The Jones' are the poorest of the Founding Families, why would I associate with them?" His face turned up in amusement at her vehement denial_

"_When have you ever rated someone based on monetary value?" he said, knowing the words held familiarity _

"_You followed us?" She said irate_

"_Don't be ridiculous, I overheard you. I was in the old woods last night as well."_

"_What were you doing in the old woods?" Stefan stared at her contemplatively. Should he tell her? Should he trust her? Why wouldn't he? She was his best friend and plus she had a secret to keep just as he did, she would understand above all others _

"_I was with Arabella."_

"_No, Arabella was at the apothecary last night." she said_

"_And who told you that?"_

"_Well I saw Miss Cordelia and she told me you told her to tell me that..." She trailed off as she caught the meaningful look on Stefan's face. She was shocked for a few seconds before her lips curled into a smirk_

"_So you and a slave girl huh? I can definitely picture it." she said to him saying it in the same nonchalant tone he had when he asked about her and William but her face shone with mischief and playfulness._

"_It just… happened."_

"_And what will Giuseppe think?"_

"_Forget about __**my**__ father, what will __**your**__ father think about both of our relationships with people of supposed lesser standing than us even though we are set to marry each other?" he said worriedly _

"_Well, neither of our fathers will find out because if my father asks I requested that Arabella accompany me last night picking flowers in the old woods when she left the apothecary." Stefan smiled at Rosalyn_

"_And William and I raced our horses in the open fields for most of the night catching up on old times." _

"_And tonight you and I are set for a moonlit stroll and I just so happen to want to bring Arabella along with." She said smirking and picking up from when he left off_

"_And if we just so happen to cross paths with William it's just fate, is it not?" he replied mirroring her smirk_

"_Of course."_

"_I love the way your mind works Ms. Cartwright."_

"_Let's face it Mr. Salvatore, even if you didn't know about William and I, you would need my cunning eventually to keep this charade up." She commented _

"_Now, would you rather chamomile or mint tea for the reception? Although that won't matter because you'll be picturing Arabella in my place the entire time." she said teasingly_

"_Oh, do shut up." He said bumping his shoulders against hers_

"_I suppose the only thing you'll want in your mouth is something of the chocolate variety."_

"_Your forwardness will be the death of you… and me." Stefan sputtered out, blushing with his eyes opened wide in shock and embarrassment _

"_No, our affairs will be the death of us Stefan." She said seriously to him with unsure eyes. It was the first time he'd ever seen her afraid. He smiled reassuringly at her_

"_Oh but what a deliciously sinful death it will be." He said to her pulling his lips into her patented smirk which she mirrored._

"_**Absolutely**__ worth it." She said back. _

_**September 12, 1863 **_

_Stefan stood on the porch bouncing on his heels impatiently. The movement was making the porch creak and despite his father's withering glances he didn't stop. He stilled himself briefly when Miss Cordelia's eyes caught his and she stared at him warningly but the smile that broke across her face when Stefan winked at her discreetly got him moving once again. Damon was coming home today and word was that he was spotted in the town square so the two other Salvatore men waited outside for his arrival. Suddenly a voice behind him made Stefan jump_

"_Is that annoying creaking necessary brother?" Damon said. Both Salvatore men whirled around to see Damon behind them leaning in the door jam. Stefan's confusion of how the elder boy managed to slip past them quickly melted as a huge smile graced his young face and he launched himself at his brother ignoring his father's disapproving grunt. Stefan knew men weren't supposed to show so much affection to each other in public but damn it he missed his brother more than he realized. Damon hugged him back laughing at Stefan's enthusiasm _

"_How did you manage to sneak past us brother?" Stefan asked when they pulled away_

"_I have my ways and I came in through the back. Happy Birthday, little brother." Damon said passing Stefan a wrapped box he had hidden behind his back. Damon nodded to his father whilst Stefan quickly opened the slightly heavy box to see a daguerreotype camera. _

_"Thank you, it's exactly what I wanted." Stefan beamed hugging Damon again_

_"Well, I wasn't completely oblivious to the hints that you were dropping in your letters. So did you miss me?" The 23 year old asked with a mischievous smirk on his face_

"_More than you know. Oh! I have so much to tell you! You'll never guess what happened! You remember the guy always sucking up to everyone, George Lockwood; well you'd be thoroughly delighted to know what a compromising position he was discovered in…" Stefan started dragging Damon off by the wrist happily and not even letting him properly greet their father. As far as he was concerned, Damon was his anyway and the longer he could keep his older brother happy and prevent him and Giuseppe from arguing and bickering, the better. Stefan pulled Damon up the stairs behind him still babbling on about how George Lockwood was not only caught in the throes with Jennifer Donovan but enacted their passion in the Fell's house. When they got to Stefan's room he put his new camera reverently on his side table and then plopped down on to his bed and looked intently at Damon with a happy smile_

"_Tell me everything. When you're not fighting what do you do? Did you make friends? Do you see new places? Tell me that something good has come from you being away?" _

_Except Arabella, Stefan thought _

"_Well, the men are all nice enough. They're from all kinds of different places and we trade stories of our towns and what we will do when we get home. I've told them fond accounts of you and Miss Cordelia and some others here in town. How has father been treating you?" He asked the last question with a concern tinged voice_

"_Fine mostly. Beatings have been minimum, though I've been forced to endure more founder's meetings than I've ever cared to but I've stayed out of the house mostly."_

"_Doing what?" Damon asked curiously_

"_Predominantly spending time with Rosalyn Cartwright… my fiancée." It wasn't complete lie, he had spent copious amounts of time with Rose. Damon's face reared back almost comically_

"_Fiancée? You mentioned no fiancée in your letters; you merely referred to her as a friend." _

"_It's our father's will, nothing we can do about it. Besides I am happily in love with Rosalyn." He said trying to sound convincing. Damon stared at him briefly before commenting_

"_Keep telling yourself that and you might start to believe it, though I doubt it. You may be in love but it's certainly not with Rosalyn." Damon said to his brother leaving no room for argument_

"_How do you do that? How do you read me like I'm an open book?" Stefan asked perturbed at his brother's easy analysis of him_

"_You're my baby brother; I've known you your whole life. To me you are an open book."_

"_Well… stop it, it's annoying and embarrassing and inconvenient… and at the moment, very dangerous." Damon narrowed his eyes at his brother_

"_What have you gotten yourself into Stefan?"_

"_I don't know if I can tell you."_

"_And why would that be?"_

"_Because I'm not the only one at risk and if I or anyone else were to hurt this other person I could never forgive myself."_

"_Brother, you know I'm always here for you. I'll help you with whatever trouble has arisen."_

"_There is no trouble… not yet anyway." Stefan looked down frowning before putting a smile on his face_

"_Let us not waste time on somber things, you've just returned home in one piece and that is to be celebrated." Damon smiled hesitantly at his brother before giving in and beaming at him._

"_I **did** miss you Stefan, you were my reason never to give up or give in."_

"_Good, I'm glad. I don't know what I would do if I lost you, fratellone, I'd probably lose myself."_

"_You won't have to worry about that anytime soon fratellino." Damon replied, affectionately ruffling Stefan's hair which he noticed had turned an even darker brown than when he last saw Stefan, his hair now was in stark contrast to his original blonde locks. He had also gotten taller and lost the awkward, lanky appearance he once had and the illusion that he couldn't control his limbs even if he tried. There was a certain glow about Stefan that was different, whatever it was it looked good on him and it made Damon happier to see Stefan so happy despite the fact that whatever the object of his happiness was also caused him great concern and alarm._

_**September 19, 1863 **_

_Damon was sitting in his room late at night using his oil lamp to read a book. There was a slight knock on the door and when he looked up there stood Stefan. He looked at him questioningly but the younger boy just beckoned him to follow him. He put his book down and followed his brother quietly as they snuck out of the house, careful to avoid any creaky floorboards. They ran in silence all the way into the security of the woods before Damon stopped Stefan._

"_What's going on Stefan? Where are we going?"_

"_I have someone I need for you to meet but before we go promise me you won't do anything rash or jump to conclusions." Stefan said seriously, Damon nodded his agreement_

"_I promise." The two trekked through the woods until they reached the picturesque clearing Damon knew well and there Damon saw a girl he vaguely had a memory of but couldn't quite place. She stood up looking at Damon nervously who stared back at her curiously. Stefan stepped between the two comfortingly putting his arm on Damon's shoulder and holding his hand out for Arabella to take, which she did._

"_Stefan, who's this?" Damon asked, flickering his eyes towards where his brother's hand was intertwined with the beautiful black girl's making their fingers resemble the pattern of a piano._

"_Damon, this is Arabella. She's my… she's the girl I'm in love with." Stefan told his brother briefly glancing lovingly towards a still nervous Arabella before flickering his cautious eyes back to his older brother._

"_Oh." Damon said. Stefan looked at his brother confused_

"'_Oh'?"_

"_Yes, 'oh'."_

"'_Oh', what exactly?"_

"'_Oh', I see why you were cautious in wanting me to meet her. It's very dangerous what you're doing and if anyone were to find out the ramifications could be ghastly." Damon said in a stern tone. The newly turned seventeen year old lovers lowered their heads like children being scolded_

"_However… seeing as how Stefan has seemed to be of much lighter spirits lately you can trust that I will guard this secret and I won't breathe it to a soul." The two looked up thankfully and Stefan beamed a smile at his brother_

"_Thank you brother." Damon smiled gently at Stefan_

"_Just be careful and Arabella?" The girl in question looked at him slightly frightened_

"_Thank you." She looked at him confused _

"_For taking care of him whilst I was gone. I'm not sure where he'd be if left him to his own devices."_

"_Hey! I am perfectly capable of caring for myself." Stefan protested to which both Damon and Arabella fixed him with very pointed looks._

"_He is very happy with you, I could tell as soon as I saw him that he had found someone special. I only wish that you two could be more open about each other but with the perilous times we live in it seems an impossibility… for now."_

"_Thank you for your support Mr. Salvatore."_

"_Mr. Salvatore is our insipid father, please call me Damon. I feel the two of us will be in each other's lives for a while to come." Arabella smiled at that and shook Damon's outstretched hand. The three sat in the clearing enjoying the nature and learning more about each other, trading stories and bonding. In that moment Stefan felt all was right in the world._

_**March 17, 1864**_

_Rosalyn lay in the hay in the barn with only a trench coat covering her and William's naked bodies. Even though six months had passed since they first found out of each other's affairs, she and Stefan still had not married so still lived with her father and she couldn't let him catch her and William. _

"_Rosie?" She heard William's calm voice say_

"_Yes?"_

"_Do you dread it?" he asked almost hesitantly_

"_Dread what?" she said turning her head to face him_

"_Dread the day where we have to face reality and give up the illusion that we could ever be together forever."_

"_Stop that talk! I said I'd never leave you… unless you—"_

"_Don't be absurd, I'd never be able to even though I should. But what will we do when you and Stefan are married? Will you two keep the charade of the perfect married couple while you love other people? Will you take Arabella to live with you two and have she and Stefan share a bed chamber together? What if you become pregnant? Are we supposed to tell the general public Stefan is the father and only refer to me as the father in private? Will we never tell the child who it's father is? What if Arabella and Stefan wish to have children? Will their children have to be locked away like savages or dirty secrets? We'd all be living in even deeper sin than we already do." William said passionately, not noticing the tears that were welling in Rosalyn's eyes_

"_You do not think I haven't thought of all of that and more. I love you with all of my heart yet I am set to marry my best friend who is playing with his life being in love with Arabella. You don't think that all of this scares me but what am I supposed to do? Can you answer any of those questions better than I or Stefan or Arabella can? All of our lives are hanging in the balance here. We cannot make any sudden decisions that won't affect both Stefan and Arabella just as much if not more than us. You and I, the only difference between us is a couple thousand dollars. The difference between Arabella and Stefan goes back 200 years. They are my family, they are important to me so no I don't have the answers to the questions you have, not any answers that will please you anyway. All I can say is that we should take this one step at a time." _

_Outside the barn Stefan stood frozen while Arabella had tears in her eyes at hearing the words of their close friends. Rosalyn and William had become brothers in arms with them while Stefan and Arabella fought their own civil war and to hear all the things that all of them had so steadfastedly ignored splayed out before them, to her all the uncertainties of the future was too much for any of their hearts to bear. What they didn't know was that someone had an inkling to their little secret and that it was about to blow up in all of their faces._

_**March 18, 1864**_

_Rosalyn and Stefan giggled and chuckled as he was in the middle of a futile attempt to win an impromptu fencing match against the blonde._

"_Your father should get a refund from whoever taught you because you're horrible." She teased_

"_No, you play dirty." He replied huffing_

"_Is there any other way to play?" she replied smirking, he glared at her playfully before lunging at her to which she easily dodged. _

"_ROSALYN!" They heard Abraham Cartwright bellow through the house. The two immediately hid the swords in the couch, knowing seeing her with the sword would only inflame her father's rage_

"_What have you done this time?"_

"_I'm not sure. When does he ever need a reason to be angered? He could be pissed off because he looked up and discovered that the sky was blue." Rosalyn quipped. The two looked up as Arabella ran in the room ahead looking horrified. They looked at her face confused before they faces fell into the same horror_

"_Which one of us?" Rosalyn asked_

"_You and William." She said, her voice betraying every bit of her terror. Rosalyn looked fearful as Abraham's footsteps got closer to the room. Stefan grabbed both Arabella and Rosalyn and opened the door to the coat closet, he shoved both girls inside before they could protest and closed and locked the door, trapping them inside as the door only opened from the outside. He moved away from the closet and schooled his expression so he could try to smooth this situation over._

"_Rosalyn!" Abraham shouted bursting into the room only to see Stefan sitting on the couch sipping out of a tea cup casually, a little too casually._

"_Mr. Cartwright." Stefan addressed formally, putting his tea cup down and getting up to bow his head respectfully at the older man_

"_Salvatore, where is Rosalyn?"_

"_Rosalyn? I'm not sure. I believe she went into town with Arabella." Stefan said putting his shaking hand behind his back. Abraham knew he knew something more than what he was saying but decided to play along with the boy in hopes he would slip up._

"_Well, I'm sorry to inform you that your fiancée, my own daughter, is running around town opening her legs at any passing fancy." Abraham said harshly walking over to the brandy and drinking it straight out of the decanter it was in._

"_Who? Rosalyn? No sir, you must've heard wrong." Stefan protested strongly, because it was a lie. She was only with William, no one else, not even Stefan. The two had only ever shared chaste, innocent kisses to please the public, nothing further._

"_Yes, it is true. She was discovered in the barn, in the throes with William Jones. I know he is a friend, I am sorry that my daughter and that poor excuse for a Founder's Family have disgraced you so. Yet…"_

"_Yet?"_

"_Yet, you do not seem so devastated." Abraham said suspiciously, while he played Stefan like a fiddle_

"_It is shock sir. Rest assured once I am able to sit down and process not one but two betrayals I will be outraged. But may I ask…"_

"_What is it boy?"_

"_What do you plan to do to Rosalyn?" Stefan asked timidly_

"_Oh well she will be sufficiently punished, don't you worry son. Once she has gotten the proper physical punishment she shall be sent far away from that Jones boy and when she has learned her lesson she may return to work for my forgiveness." Abraham relayed matter-of-factly_

"_Sir, Rosalyn…" Stefan looked down and breathed deeply to calm himself. He would gladly throw himself under the bus for Rosalyn but he wouldn't put Arabella at risk, he closed his eyes and shook his head to get his bearings_

"_Rosalyn should not be held accountable for looking for love elsewhere. I-It was I who strayed from her long before William was a thought in her head. I told her she should be with William. If not for me your daughter's virtues would never be questionable to you sir." Stefan looked up at the reddening face of Abraham Cartwright. _

"_I fully expect due punishment for my indiscretion against your daughter and the distress I have caused your family." Stefan said, inwardly steeling himself for the pain that was sure to come_

"_Strayed to who?" Abraham sneered at him_

"_No one of importance." Stefan said after a beat of silence. Cartwright didn't seem to care he lunged at Stefan and punched the young boy in the jaw sending him reeling back. He then punched him twice in the gut and kneed him in the groin sending him to his knees. He grabbed Stefan by his hair and dragged him outside while some of the servants and slaves watched this fearing for the young boy who was still so naïve in many ways. Two of the child servants scurried away from the fray and ran out the back towards the Salvatore Estate to get Giuseppe, they saw Cartwright grab the whip on his way outside and they feared he would kill Stefan._

_Abraham dragged Stefan to the open field and ordered two slaves to hold his arms as he was forced on to his knees. Cartwright got behind Stefan and paid no mind to the group of slaves and servants who served as an audience_

"_This is for my daughter you insolent, traitorous cur." He sneered, before longing out the whip cracking it back through the air and slashing it against a disoriented Stefan's back, who screamed in pain. The whip was worn and taped so it didn't tear skin or rip his shirt open, it was much like being beat with a belt. However, Cartwright hit him in the same places more than once which was causing his back to welt and turn red and begin to bleed beneath his shirt. _

_From inside the house, Rosalyn and Arabella screamed trying to alert someone to their presence in the closet. They could hear Stefan from outside and desperately wanted to help him. Suddenly someone pulled open the door and they saw the pale face of a ginger girl who was one of Rosalyn's handmaidens. She pointed towards outside and the two immediately made a beeline for the door and pushed through the masses to see a sight that stopped their hearts. Abraham was whipping Stefan unrelentingly and there were spots in the back of Stefan's white shirt where you could see blood stains, Stefan's face was contorted in pain and tears were slipping down it, all the slaves and servants looked horrified and/or sympathetic._

"_FATHER, STOP!" Rosalyn screamed. Abraham stopped and turned to see his daughter's tear stricken face and her sorrowful expression_

"_No, I will not. He put you in a position where your virtues, womanhood and social status were made forfeit."_

"_He didn't hold a bayonet to my head and force me to do anything. It was all my choices, you cannot punish him for that."_

"_Oh you will get yours in due time girl." He spat at her, before slapping her across the face. He looked back at Stefan to continue raging at him and then noticed Arabella crouched in front of him holding his face in her hands tenderly kissing tears off of his face and comforting him._

"_WHAT IS THIS BLASPHEMY!?" Abraham bellowed slapping the whip between the two hitting Arabella in the chest and forcing her back_

"_You strayed from my daughter for a slave girl!? For someone less than human!? You ungrateful little—",_

"_Mr. Cartwright, the fault is all my own." Arabella said speaking up._

"_I seduced him using magic. It was not his fault that he gave in." she said_

"_No! No! She's lying! Do not believe her! It was my fault not hers or Rosalyn's." Stefan protested_

"_Father, do not hurt her." Rosalyn warned moving to stand by Stefan who was still on his knees with his arms being held._

"_Oh I won't hurt her…" He said walking over to the girl who looked into his face bravely, knowing that she only had seconds. He pulled her up and then everything happened faster than anyone could register. He caressed her face and then reached for something in his pocket before anyone could react or foresee what would happen there was a flash as if something was reflecting the sun. There was a red liquid that flew through the air and a scream from one of the servants that pierced the stillness followed by a series of shouts, hollers, gasps and cries when everyone realized that he had slashed Arabella's throat and she was holding her neck as blood gushed over her hand unrelenting. Rosalyn and Stefan screamed and shouted in horror and grief not able to remove their eyes from her. She fell to her knees and switched her eyes to Stefan's staring at him before she fell flat on her face and breathed her last breathe._

_**March 25, 1864**_

_Stefan lay motionless in his bed with the blinds drawn blocking out the sun, the covers pulled up to his waist and tears falling silently from his eyes which were red and sore from all the crying he had done. It seemed he hadn't stopped at all since the moment Arabella's body hit the ground, bloodied and devoid of life. He had cried while holding her body, he cried when a couple of white servants instead of his father showed up to calm Mr. Cartwright and ensure Stefan lived, he cried when he and Rosalyn snuck out to bury Arabella properly and he cried when Rosalyn was shipped off to London by her father to get her away from both William and Stefan. He had been locked up in his room for days and somehow his father was oblivious to all that had happened but then again he had been busy preparing for their special guest, Katherine Pierce to arrive in two months, that he hardly paid Stefan any mind. Plus, Cartwright had his servants and slaves on lock so they wouldn't say anything and the Salvatore servants feared Cartwright as much as his own servants did. _

_Suddenly, there was a knock on his bedroom door but he didn't say anything or make a move to answer it, he knew the person would just walk on, they had no idea what Stefan's problem was and they wouldn't ask. To Stefan's surprise the door opened and in walked Miss Cordelia. He didn't say anything about her being in his room or move but his eyes followed as far as they could as she locked the door, walked over to the window and drew back the curtains allowing the sunlight to fill the room and shower on Stefan. He pulled the sheets over his head to block the light from assaulting his eyes. _

"_None of that Stefan. You haven't left this room in four days, you haven't eaten or talked to anyone or gotten any fresh air. You get on up out of that bed now, ya hear." She said in her voice full of southern twang and inflection_

"_I'm not leaving." Stefan said in his hoarse, barely audible voice_

"_What is the matter with you boy? Is this about Damon or Rosalyn?"_

"_No." He answered reluctantly as he felt the bed dip next to him, signaling that Cordelia was sitting next to him_

"_Your father?"_

"_No."_

"_Talk to me Stefan, what's eating away at you?" She asked in a soft, maternal voice that made Stefan sob before taking the covers away from his face. She gasped softly as she took in his tired, bloodshot, dull eyes with the purplish bruises underneath them from lack of sleep, tears falling from them only made him look even worse and his jaw was slightly bruised like someone had punched him _

"_Stefan, what happened to you?" He looked around the room making sure the door was locked as he held his hand to his mouth trying, to no avail, to contain his sobs _

"_Arabella's dead." He told her through the tears_

"_What? What do you mean she's dead?"_

"_It's my fault."_

"_No Stefan, I'm sure whatever happened wasn't your fault." She told him as tears collected in her eyes, she had always been fond of Arabella and to hear that she was dead felt like her soul was being cut in half._

"_Cordy… we were together. We were… we were in love. I love—I loved her. Rosalyn was with William and I was with Arabella and we were hiding but someone found out about her and William and I took the fall for her. I told her father that I forced her to be with William, that I gave her no choice because I cheated on her and Mr. Cartwright was punishing me but he found out about me and Arabella and he killed her right in of me and Rosalyn. He slashed her throat."_

"_Oh dear lord." Cordelia breathed, holding a hand to her chest as she felt her heart beating wildly against her rib cage like it was about to pump right out of her chest. _

"_What about her body?" Cordelia asked quietly _

"_Rosalyn and I buried her before she left."_

"_You said Cartwright punished you?" Stefan sat up and slowly and carefully took his shirt off as his back still ached, he took the crudely applied bandage off and turned to show her his back. She gasped as there she saw the red and pink welts all of over his back as well as some lashes. She had of course seen worse but never really seen someone whip a white child like this. _

"_Stefan, why didn't you come to me? These could of festered and you could've died."_

"_I didn't care." He told her truthfully_

"_I wish I was dead and Arabella was alive, I wish I could take her place. I failed her, I don't care if I die." Cordelia got up and left the room. When she returned she had fresh bandages, hydrogen peroxide and a soft cloth. She sat back down on the bed and began working on his back. _

"_Stefan, you didn't fail her. The world just wasn't ready for the two of you yet. She's a black slave with no parents and you're the white son of one of the wealthiest men in Virginia, a founding family no less. I'm sorry darling but I don't know how you two would've worked out. I wish she wasn't dead, lord knows I do, but I couldn't bear it if you died too. With Damon away in that stupid war getting shot at and seeing death all around him and having to kill people and Arabella's dead now, you're the only one I got right now sweetheart you can't go away too, you hear?" She told him earnestly while cleaning the wounds and then bandaging them before she wrapped her arms around his shoulders and hugged him from behind. _

"_I know, I have 'responsibilities'." Stefan said begrudgingly, leaning his head back on the shoulder of the woman who had raised him_

"_Does your father know about this?" Stefan shook his head 'no' and Cordelia sighed in relief _

"_And you know what? He's never going to know because we're going fix you up and you're going focus on Miss Pierce's arrival and your brother coming back soon and that's what matters right now, alright?" Stefan nodded to Cordelia but truthfully he didn't want to let this go, he wanted to rage and scream and curse the world and burn the entire town to the ground, he wanted to curl into a ball and cry his heart out and wither away and die. However, that would be selfish and god forbid Stefan were ever that, so maybe Cordelia was right, maybe what he needs is distraction and maybe Katherine Pierce can be that distraction. His father's been hinting that he was glad that Stefan and Rosalyn's engagement was over because Stefan could have a chance with Katherine so maybe he should just let it happen, let himself be miserable with a woman who he won't ever love as much as Arabella because her death deserves retribution and perhaps he's the one who should pay, him and everyone else in this town, especially the founding families but he can't make them pay yet, himself however he could make sure was miserable._

_**PRESENT DAY**_

"After that I met Katherine and Damon came back and the rest was history I suppose." Stefan said ending his tragic story with a sorrowful look on his face. Caroline had tears in her eyes for him and Arabella and Klaus had a solemn look on his face.

"What, what ever happened to Rosalyn?" Caroline asked him

"She… came back a month after we met Katherine and I was ecstatic and I started spending more time with her than with Katherine and Katherine I guess wasn't satisfied with just having Damon at her side. She didn't just compel me to stay away from Rosalyn, she killed her. I guess she got an impression of how much sway Rosalyn had over me because if Rosie had told me to I would've stayed away from Katherine. William ended up marrying Jennifer Donovan so technically he's Matt's great, great, great grandfather." Stefan relayed to them.

"Oh gosh Stefan, I'm so sorry I shouldn't have asked." Caroline said throwing her arms around his shoulder and pulling him into a hug.

"No, it's okay. I've only ever spoken about it once in the last 145 years. I never told Damon the truth about what happened to Arabella and I never even told Katherine she existed, the only person I told was Lexi."

"And us." Klaus said silently

"It's appropriate I suppose. The only people who knew about that secret was my best friends and it still rings true to this day." Stefan said as he felt Caroline's arm tighten around him and Klaus smile a small smile at him. He had caught the meaning, Klaus and Caroline were Stefan's best friends and as Stefan's best friends the two knew Stefan obviously wasn't over what happened to Arabella but they'd help him through it, they always would be there for him through anything and this was definitely no exception.

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